Organic syntheses via transition-metal complexes. 110.1 A convenient regio- and stereoselective approach to the angular allylation of bicyclic cyclopentadienes generated by the (1-alkynyl)carbene complex route

Organometallics

Volumn 20, Issue 11, 2001, Pages 2183-2190

  Wu, He Ping ^a   Aumann, Rudolf ^a   Fröhlich, Roland ^a   Wegelius, Elina ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLCARBENE COMPLEX; ALLYLAMINES; ALLYLATION; ALLYLTETRAHYDROPENTALENYLIDENEAMINES; BICYCLIC CYCLOPENTADIENES; PYRIDINE;

ADDITION REACTIONS; ALCOHOLS; AMINES; CARBOXYLIC ACIDS; COMPLEXATION; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

TUNGSTEN COMPOUNDS;

EID: 0035963232     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010045o     Document Type: Article

References (27)

1. For part 109 see: Göttker-Schnetmann, I.; Aumann, R. Organometallics 2001, 20, 346-354.
2. For a recent review see: Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242.
3. (a) Meyer, A. G.; Aumann, R. Synlett 1995, 1011-1013.
4. (b) Aumann, R.; Meyer, A. G.; Fröhlich, R. Organometallics 1996, 15, 5018-5827.
5. (c) Aumann, R.; Kössmeier, M.; Zippel, F. Synlett 1997, 621-623.
6. (d) Aumann, R.; Kössmeier, M.; Jäntti, A. Synlett 1998, 1120-1122.
7. (e) Aumann, R.; Kössmeier, M.; Mück-Lichtenfels, Ch.; Zippel, F. Eur. J. Org. Chem. 2000, 37-49.
8. For the basics of this π-cyclization reaction see: (a) Aumann, R.; Heinen, H.; Hinterding, P.; Sträter, N.; Krebs, B. Chem. Ber. 1991, 124, 2343-2347.
9. (b) Aumann, R.; Heinen, H.; Hinterding, P.; Sträter, N.; Krebs, B. Chem. Ber. 1991, 124, 1229-1236.
10. For a recent review on 1-metalla-hexatrienes see: Aumann, R. Eur. J. Org. Chem. 2000, 17-31.
11. de Meijere, A. Pure Appl. Chem. 1996, 68, 61.
12. Aumann, R.; Göttker-Schnetmann, I.; Fröhlich, R.; Meyer, O. Eur. J. Org. Chem. 1999, 2545-2561, 3209.
13. Aumann, R.; Fröhlich, R.; Prigge, J.; Meyer, O. Organometallics 1999, 18, 1369-1380.
14. Aumann, R.; Göttker-Schnetmann, I.; Fröhlich, R.; Saarenketo, P. Chem. Eur. J. 2001, 7, 711-720.
15. Wu, H.; Aumann, R.; Wibbeling, B. Eur. J. Org. Chem. 2000, 1183-1192.
16. Wu, H.; Aumann, R.; Fröhlich, R.; Saarenketo, P. Chem. Eur. J. 2001, 7, 700-710.
17. Wu, H.; Aumann, R.; Fröhlich, R.; Wegelius, E.; Saarenketo, P. Organometallics 2000, 19, 2373-2381.
18. Wu, H.; Aumann, R.; Venne-Dunker, S.; Saarenketo, P. Eur. J. Org. Chem. 2000, 19, 3463-3473.
19. For related studies, in which 1-metalla-1,3,5-trienes were generated by addition of dienes to (1-alkynyl)carbene complexes, see: (a) Barluenga, J.; Aznar, F.; Barluenga, S.; Fernández, M.; Martin, A.; García-Granda, S.; Pinera-Nicolás, A. Chem. Eur. J. 1998, 4, 2280-2298.
20. (b) Barluenga, J.; Aznar, F.; Palomero, M. A.; Barluenga, S. Org. Lett. 1999, 541.
21. Wu, H.; Aumann, R. Results to be published.
22. For details see the Supporting Information.
23. Data sets were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator, Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, A.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction SORTAV
24. Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37.
25. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426, structure solution SHELXS-97
26. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473, structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997).
27. For a more detailed NMR study of this dynamic process see ref 8.